ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid (CFc000117399)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:39:59 UTC

Chemfont ID

CFc000117399

Molecule Identification

Common Name

3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(e)-2-(4-methoxy-2-oxo-2h-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 6-[(e)-2-(2,3-dihydroxy-4-methoxyphenyl)ethenyl]-4-methoxy-2h-pyran-2-one. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-{2-hydroxy-6-methoxy-3-[(e)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₁H₂₂O₁₂

Average Molecular Weight

466.395

Monoisotopic Molecular Weight

466.111126148

IUPAC Name

3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-6-oxopyran-2-yl)ethenyl]phenoxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=C(O)C(OC2OC(C(O)C(O)C2O)C(O)=O)=C(OC)C=C1)C1=CC(OC)=CC(=O)O1

InChI Identifier

InChI=1S/C21H22O12/c1-29-11-7-10(31-13(22)8-11)5-3-9-4-6-12(30-2)18(14(9)23)32-21-17(26)15(24)16(25)19(33-21)20(27)28/h3-8,15-17,19,21,23-26H,1-2H3,(H,27,28)/b5-3+

InChI Key

AHOAJOGWHSAZPW-HWKANZROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Methoxybenzene
Phenoxy compound
Phenol ether
Styrene
Anisole
1-hydroxy-4-unsubstituted benzenoid
Beta-hydroxy acid
Phenol
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Hydroxy acid
Monosaccharide
Benzenoid
Pyran
Oxane
Heteroaromatic compound
Vinylogous ester
Secondary alcohol
Lactone
Polyol
Acetal
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0136990)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.12 g/L	ALOGPS
logP	0.71	ALOGPS
logP	-0.073	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.07	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	111.18 m³·mol⁻¹	ChemAxon
Polarizability	44.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0136990

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid (CFc000117399)

MOL for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

3D MOL for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

3D SDF for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

3D-SDF for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

PDB for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

3D PDB for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

SMILES for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

INCHI for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

Structure for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)

3D Structure for CFc000117399 (3,4,5-trihydroxy-6-{2-hydroxy-6-methoxy-3-[(E)-2-(4-methoxy-2-oxo-2H-pyran-6-yl)ethenyl]phenoxy}oxane-2-carboxylic acid)